2-Amino-5-cyanopyridine → 2-(5-Bromofuran-2-yl)-imidazo[1,2-a]pyridine-6-carbonitrile

HRID 2113554노트

반응식

HRID 2113554 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Br[CH2:11][C:12]([C:14]1[O:15][C:16]([Br:19])=[CH:17][CH:18]=1)=O>C(O)C>[Br:19][C:16]1[O:15][C:14]([C:12]2[N:1]=[C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]3[CH:11]=2)=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 8182602-Amino-5-cyanopyridineHCID 125376692-Bromo-1-(5-bromofuran-2-yl)ethan-1-one

생성물 1

HCID 692538532-(5-Bromofuran-2-yl)-imidazo[1,2-a]pyridine-6-carbonitrile수율 74%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 6-Amino-nicotinonitrile (1.19 g, 10 mmol) and 2-Bromo-1-(5-bromofuran-2-yl)-ethanone (2.66 g, 10 mmol) in ethanol (50 mL) was refluxed for 24 h. The precipitate was filtered and neutralized with aqueous NaHCO3 solution. The precipitate was filtered and dried to furnish 3a in 74% yield, mp 212-214° C. (EtOH). 1H NMR (DMSO-d6); δ 6.75 (d, J=3.6 Hz, 1H), 6.98 (d, J=3.6 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 8.29 (s, 1H), 9.30 (s, 1H). 13C NMR; δ 150.5, 144.2, 137.3, 134.3, 125.4, 121.9, 117.2, 116.9, 113.9, 110.4, 109.8, 97.2. MS (m/z, rel.int.); 288 (M+, 100), 161 (8). Anal. Calcd. for 3a (C12H6BrN3O): C % 50.03, H % 2.10. Found: C % 49.97, H % 2.17.

후처리

  1. temperaturewas refluxed for 24 h
  2. filtrationThe precipitate was filtered
  3. filtrationThe precipitate was filtered
  4. customdried

출처 및 근거

ORD 기록
ord-cca7e578d3e5470bacc2afa162f0338b
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432278B2

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